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Palladium-catalyzed arylation of alpha,alpha-disubstituted arylmethanols via cleavage of a C-C or a C-H bond to give biaryls.
J Org Chem. 2003 Jun 27; 68(13):5236-43.JO

Abstract

The palladium-catalyzed arylation of alpha,alpha-disubstituted arylmethanols with aryl halides proceeds not only via C-H bond cleavage at the ortho-position, but also via cleavage of the sp(2)-sp(3) C-C bond with the liberation of ketones (beta-carbon elimination) to give the corresponding biaryls. Both reactions appear to occur through common arylpalladium(II) alcoholate intermediates. The results of systematic studies with respect to which C-C or C-H bond is preferentially cleaved in the arylation are reported. Among the important findings is the selective elimination of ortho-substituted aryl groups even from aryl(diphenyl)methanols due to steric reasons. Thus, various biaryls having ortho-substituents can be produced efficiently by treatment of the corresponding aryl(diphenyl or dimethyl)methanols with aryl bromides and chlorides.

Authors+Show Affiliations

Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

12816483

Citation

Terao, Yoshito, et al. "Palladium-catalyzed Arylation of Alpha,alpha-disubstituted Arylmethanols Via Cleavage of a C-C or a C-H Bond to Give Biaryls." The Journal of Organic Chemistry, vol. 68, no. 13, 2003, pp. 5236-43.
Terao Y, Wakui H, Nomoto M, et al. Palladium-catalyzed arylation of alpha,alpha-disubstituted arylmethanols via cleavage of a C-C or a C-H bond to give biaryls. J Org Chem. 2003;68(13):5236-43.
Terao, Y., Wakui, H., Nomoto, M., Satoh, T., Miura, M., & Nomura, M. (2003). Palladium-catalyzed arylation of alpha,alpha-disubstituted arylmethanols via cleavage of a C-C or a C-H bond to give biaryls. The Journal of Organic Chemistry, 68(13), 5236-43.
Terao Y, et al. Palladium-catalyzed Arylation of Alpha,alpha-disubstituted Arylmethanols Via Cleavage of a C-C or a C-H Bond to Give Biaryls. J Org Chem. 2003 Jun 27;68(13):5236-43. PubMed PMID: 12816483.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Palladium-catalyzed arylation of alpha,alpha-disubstituted arylmethanols via cleavage of a C-C or a C-H bond to give biaryls. AU - Terao,Yoshito, AU - Wakui,Hiroyuki, AU - Nomoto,Michiyo, AU - Satoh,Tetsuya, AU - Miura,Masahiro, AU - Nomura,Masakatsu, PY - 2003/6/21/pubmed PY - 2003/6/21/medline PY - 2003/6/21/entrez SP - 5236 EP - 43 JF - The Journal of organic chemistry JO - J Org Chem VL - 68 IS - 13 N2 - The palladium-catalyzed arylation of alpha,alpha-disubstituted arylmethanols with aryl halides proceeds not only via C-H bond cleavage at the ortho-position, but also via cleavage of the sp(2)-sp(3) C-C bond with the liberation of ketones (beta-carbon elimination) to give the corresponding biaryls. Both reactions appear to occur through common arylpalladium(II) alcoholate intermediates. The results of systematic studies with respect to which C-C or C-H bond is preferentially cleaved in the arylation are reported. Among the important findings is the selective elimination of ortho-substituted aryl groups even from aryl(diphenyl)methanols due to steric reasons. Thus, various biaryls having ortho-substituents can be produced efficiently by treatment of the corresponding aryl(diphenyl or dimethyl)methanols with aryl bromides and chlorides. SN - 0022-3263 UR - https://www.unboundmedicine.com/medline/citation/12816483/Palladium_catalyzed_arylation_of_alphaalpha_disubstituted_arylmethanols_via_cleavage_of_a_C_C_or_a_C_H_bond_to_give_biaryls_ DB - PRIME DP - Unbound Medicine ER -
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